By 1967, Harry landed a recording contract with RCA Records. His first album, called "The Pandemonium Shadow Show" featuring witty lyrics and a Beatles medley called "You Can't Do That", was a commercial flop, but received good critical notices. More importantly, it attracted the attention of The Beatles themselves. John Lennon and Paul McCartney cited Nilsson as one of their favorite artists while addressing the media at the launching of their Apple label. Lennon even phoned Nilsson to congratulate him on the album. Nilsson quit his job at the bank the very next day and turned his attention to music.
Three Dog Night boosted Harry's career even further when they took his song, "One" into the Top Ten in 1969, and Nilsson's second LP, "Aerial Ballet" began to get more attention. Two months later, "Everybody's Talkin'" was chosen as the theme for the film Midnight Cowboy, and suddenly, Harry Nilsson had his own Billboard #6 hit, one that would win a Grammy Award. The irony was that, although Nilsson was primarily identified as a singer/songwriter, the song was actually written by Folk-Rock artist Fred Neil.
Harry also provided the soundtrack for a film by Otto Preminger, called Skidoo, which turned out to be the very last outing for Groucho Marx. He also wrote scores for other films and composed the catchy theme to the TV show The Courtship of Eddie's Father. Nilsson was never one to be content to stay within definite categories, as demonstrated by two albums he released in 1970. The first was devoted entirely to covers of songs by Randy Newman (then just emerging as a performer). Another was his soundtrack to an animated children's special, The Point, which included the #36 hit "Me and My Arrow" in 1971. Oddly enough, it was a cover of yet another artist's song, (Badfinger) that gave Nilsson his biggest hit single. "Without You" (#1) appeared on the album, "Nilsson Schmilsson", which included a couple of other minor hits, "Jump into the Fire" (#27) and "Coconut" (#8). During the first half of the 1970s he continued to broaden his range from the well-crafted, peppy, sensitive tunes that had dotted his early releases, cutting some tougher, more sour work. The album "Son Of Schmilsson" was released while its predecessor was still on the charts, and Harry found himself competing with his own work. Despite this, the LP reached #12 on the Billboard 200 chart and spawned the #23 hit, "Spaceman". The follow-up single, "Remember (Christmas" stalled at #53, and the next release, "Joy", failed to chart at all.
He lost some of his edge, however, with 1973's "A Little Touch of Schmilsson in the Night", a collection of Pop standards with an orchestra conducted by arranger Gordon Jenkins (most noted for his work with Frank Sinatra). His affection for the music wasn't entirely surprising, as there had always been a strong Tin Pan Alley flavor to much of his writing, but, with Disco music on the horizon, it wasn't exactly in step with the times.
Much of Nilsson's notoriety came from a period in the mid-1970s when he was a drinking buddy of John Lennon in Los Angeles (where Lennon was living during a separation from Yoko Ono). The drunken pair were thrown out of L.A.'s Troubadour club in a well-publicized incident after disrupting The Smother's Brothers act. Lennon offered to produce Nilsson's next album. The timing could not have been worse, as Nilsson lost his voice during the sessions, rupturing one of his vocal cords, keeping it a secret out of fear that Lennon would abandon the project. Released as "Pussycats", it was his last album to make the Hot 100. During the same period, he also embarked on a project with another L.A. based ex-Beatle, Ringo Starr, acting and writing music for the little-seen film, Son of Dracula. The movie was generally regarded as a failure despite a strong cast (starring Ringo) and great songs. One tune from the soundtrack, "Daybreak", became Harry's last charting single when it topped out at #39 in the Fall of 1974.
Harry's voice had been damaged by his hard living and he croaked his way through recording sessions with a bleeding throat. It was amazing he could do anything at all with what was left, let alone complete another album. This new chapter of the Nilsson story continued with two more L.A. session-men albums "Duit on Mon Dei" (formerly God's Greatest Hits) and "Sandman", by which time the voice was recovering much of its former power and warmth. The session men were gone in time for Harry's last RCA album "Knillssonn", a Pop album with orchestral backing. This delightful collection of songs was simply not publicised by an indifferent RCA and so never hit its deserved heights. Harry left RCA somewhat disillusioned. He was only ever to make one more full studio LP, 1979s "Flash Harry", which was never even released in America. The rest of his life, Harry spent with his wife Una and their ever-growing army of children. Soundtracks for Disney's Popeye movie and contributed songs to various other films and records were all the world was offered while Harry devoted a lot of his time and energy into promoting the Campaign To End Handgun Violence after his friend John Lennon was shot in 1980.
In the early '90s, Harry's health deteriorated rapidly. First diagnosed a diabetic, he later had a major heart attack and died peacefully in his sleep of heart failure in 1994, just after finishing the vocal tracks for a new album that would never be released. In 1995, various artists, including Ringo Starr, Stevie Nicks, Victoria Williams and The B-52's Fred Schneider, paid tribute to Nilsson on the LP, "For the Love of Harry". That same year, RCA released the 2-CD anthology, "Personal Best".
In 2006, a documentary called Who is Harry Nilsson? (And Why Is Everybody Talkin' About Him) was shown at the Seattle International Film Festival, the Santa Barbara Film Festival and the 7th Annual Mods & Rockers Film Festival. The movie was re-released on September 17th, 2010 with newly added, rare footage of Nilsson, extra interviews and family photos. A DVD version followed in October.